Buy Now: Sperry Top-Sider Gold Cup Shoes

All boat shoes are not made alike—like everything you wear these days, details matter. Sperry Top-Siders' Gold Cup line upgrades the classic two-eye with buttery leathers, super-smooth deerskin linings and contrast trim and laces. There's also a selection of wingtips, chukka boots and loafers with equally excellent styling, and soles that are built to reduce shock and vibration—but they'll never make you look too sensible.
Pictured: Authentic Original Chukka, $170 at sperrytopsider.com